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How to Get to the Top as a Freelancer and Stay There, According to Veterans

Archive: This article was originally published by Mediabistro around 2012. It is republished here as part of the Mediabistro archive.

Ever flip through your favorite magazines and notice the same bylines in every issue? Like, a writer who penned a Brett Favre profile for GQ also has a feature in Vanity Fair the same month, or that A-list writer who seems to get every cover story for Esquire, Essence and O.

Well, while it might appear that top editors and writers have a secret club where they’ll only work with each other, the truth is no one starts his career writing for Rolling Stone or New York. The five veteran scribes we spoke with say it takes years to build up a reputation and the trust of mega magazines ___ and once they got to the top, there are several key things they did to stay there.

“If you haven’t read three to six issues, you’re not ready to pitch.” — Aliya S. King

King’s ascent in the freelance hierarchy is a unique one. The contributor to Vibe, Essence and Latina (just to name a few) started off her professional career as a teacher. King eventually decided to focus on her writing career and has three books to her name, including the 2008 Faith Evans memoir, Keep the Faith.

Often doling out advice to aspiring freelancers on her website, King’s first piece of advice is a simple one. “Before you even think about sending a pitch to a new magazine, make sure you have done your homework ahead of time,” said King. “If you haven’t studied the magazine for three to six months, you aren’t ready to pitch the magazine and you’re probably not going to have success with it.”

While there’s no consensus on how to pitch, most of the veterans we spoke with agree that new freelancers or those pitching an outlet for the first time should err on the conservative side by including as much detail as possible. “I don’t do informal pitches,” said King. “And sometimes, I’ve worked as an editor as well, and I’ve never appreciated someone sending me an email saying, ‘Hey, I’m thinking about writing a story about this. What do you think?'”

“Pay attention to formatting.” — Daniel Duane

Daniel Duane, contributing editor for Men’s Journal, contributor to Bon App_?tit and New York Times Magazine, and author of several books, followed a similar approach by hitting the newsstands and buying any magazine that he was interested in writing for. “I think there were a couple of years where I probably subscribed to 15-20 magazines at any time,” he said. “It’s not like I read every word of every one, but every single one that came, I read the table of contents, looked at the format of the stories and thought about the format. You want to be able to develop that feel.”

“You will have communicated something neat, which is I get it. That alone is a big success, just to show that you’re really paying attention.”

Duane says that paying close attention to the details could be considered a win, even if an editor passes on your pitch. “Let’s say you finally got an editor at Islands magazine to actually pay attention to your pitches. You’ve been calling them, and you sent them emails, and you finally sent an email with some pitches. You have their attention for the moment and here’s your great Orkney Islands pitch, not knowing they are about to do an Orkney Islands double issue.” Although they will likely pass on your idea, he says, “you will have communicated something neat, which is I get it. I totally get your magazine and I totally get what you’re looking for. That alone is a big success, just to show that you’re really paying attention.”

“Focus on producing quality copy on a consistent basis.” — Mike Sager

Dubbed the “beat poet of American journalism,” Mike Sager entered the freelance magazine world in 1984 after working at the Washington Post. The 2010 winner of the American Society of Magazine Editors’ National Magazine award for profile writing is a writer-at-large for Esquire, a former writer-at-large for GQ, and former contributing editor for Rolling Stone.

Yet, Sager is probably best known for his Rolling Stone feature on the late porn star John Holmes and his role in the 1981 Wonderland murders. Instead of worrying why he was only getting $2,000 from Rolling Stone for a story that took him eight months to complete, Sager focused on making it a great story.

“You have to think about every piece being as amazing as you can make it,” he explained. “I don’t get to always choose what I do, but I just think I’m going to kick the ass of any assignment that I get because I got it and my name is going on it. Then the money follows.”

The money truly did follow for Sager as his piece on Holmes served as the inspiration for a pair of Hollywood blockbusters in Boogie Nights and Wonderland. “Over time, that $2,000 has translated into a lot more, but at the time, that’s not what I’m thinking about. At the time, I’m thinking about the work.”

“Don’t pester editors that much.” — Anthony DeCurtis

If Anthony DeCurtis has learned anything about staying power over his 30 years as a freelance writer, it’s the importance of being likeable. “One thing I do is I don’t pester editors that much,” said the Rolling Stone regular, University of Pennsylvania English professor, and author of several books, including Rocking My Life Away: Writing About Music and Other Matters. “If I have an idea that I think is good for them, whether I’m going to be doing it or not, I’ll just pass it along to them. I just try to be as cooperative and reliable as I can be.”

Sager agrees. “Don’t give them any more reason to hate you than they already have,” he said, quoting one of his mother’s favorite sayings.

Remember, you’re selling more than just your words. “The cost of a story to a magazine is only partly the check they are going to write you,” said Duane. “It’s also what you’re going to put them through. Work to be low maintenance.”

“You have to think about every piece being as amazing as you can make it.”

“Have diverse ways that you’re getting paid.” — Kelley L. Carter

Nearly two years ago, Kelley L. Carter’s world was turned upside down. USA Today laid off the Emmy Award-winning entertainment journalist, leaving the longtime newspaper reporter to ponder what her next move would be. “Freelance for me was not supposed to be a career; it was supposed to be something to do in the interim until I got my next full-time job,” said Carter. Before she knew it, Carter had received enough phone calls from editors at MTV.com, ESPN.com, Ebony and Jet and was doing better financially than she was as a full-time newspaper employee.

If you want to avoid chasing paychecks, she says, find outlets with various payment schedules. “Fortunately, I have a couple of people that pay me direct deposit. Some pay direct deposit once a month. Some pay every week. And then I still get paper checks mailed to me too, so I’m never necessarily reliant on one form of money to come in at one particular time,” she explained. “That’s what has made this whole thing on the financial side of it less of a headache.”

And if you’ve been consistent with your work and feel you’re due for a pay bump, ask for it. Freelancers with beaucoup bylines know that many editors will make exceptions (or fight for) those writers they feel are worth it. “Some editors are so protective of their budgets,” said DeCurtis. “There’s always money around. You can shake it out of people. The more established you get, the easier it is to have those conversations. It never hurts to bring it up.”

“Find the story that only you can write.” — Aliya S. King

King is an advocate of sometimes dialing down expectations and writing the story that fits you. “Find a story that only you can write,” she said. “Maybe it has something to do with where you’re from, or something to do with an artist you have a relationship with, or something to do with something that you’re particularly well equipped to write about.”

Duane had a recent conversation with a former college basketball player turned writer who was looking to stand out in his pitches. “I said, ‘There’s your subject,'” he recalled. “First of all, there has to be some great personal essay he can tell about his four years, some game that was heartbreaking to lose. That’s a world that that guy knows and we are interested in. A lot of us have areas of interest or passion that we don’t even realize we have or even occur to us.”

Part of what gives the veterans we spoke with such longevity is they’ve carved out a niche. For King, DeCurtis and Carter, it was music and entertainment. For you, it might be women’s health or college football. Write what you know, be consistent and easy to work with, and it might be your byline in all the books.

NEXT >> 7 Things They Don’t Tell You About Freelancing


Marcus Vanderberg is co-editor of FishbowlLA.

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